New azole derivatives of [17(20)E]-21-norpregnene: Synthesis and inhibition of prostate carcinoma cell growth.
Azoles
CYP17A1 inhibitors
LNCaP prostate carcinoma cells
PC-3 prostate carcinoma cells
[17(20)E]-21-Norpregnenes
Journal
Steroids
ISSN: 1878-5867
Titre abrégé: Steroids
Pays: United States
ID NLM: 0404536
Informations de publication
Date de publication:
07 2019
07 2019
Historique:
received:
14
05
2018
revised:
09
08
2018
accepted:
14
08
2018
pubmed:
28
8
2018
medline:
19
5
2020
entrez:
28
8
2018
Statut:
ppublish
Résumé
A number of isoxazole, 1,2,3-triazole, tetrazole, and 1,2,4-oxadiazole derivatives of [17(20)E]-21-norpregnene comprising 3β-hydroxy-5-ene and 3-oxo-4-ene fragments were prepared. Among the key steps for the synthesis of isoxazoles, 1,2,3-triazoles, and tetrazoles were (i) 1,3-dipolar cycloaddition of nitrile oxides or azides to acetylenes or nitriles and ii) dehydration of 17β-hydroxy-17α-methylene-azoles to [17(20)E]-21-norpregnene derivatives. 1,2,4-Oxadiazoles were prepared through the formation of acetimidamides. Potency of the synthesized compounds to inhibit CYP17A1 and to suppress growth of prostate carcinoma cells was investigated. Among the new azole derivatives, four compounds were found possessing high anti-proliferative activity.
Identifiants
pubmed: 30149075
pii: S0039-128X(18)30156-9
doi: 10.1016/j.steroids.2018.08.004
pii:
doi:
Substances chimiques
(17(20)E)-21-norpregnene
0
Antineoplastic Agents
0
Azoles
0
Norpregnadienes
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
10-18Informations de copyright
Copyright © 2018 Elsevier Inc. All rights reserved.